Of All The Bars
by Sapphire Pirate
Summary: 1940s AU. Castiel is the owner of a bar and is quite happy with his life until one of his customer's brother literally runs back into his life. Casablanca-esque AU based on the one on Tumblr where Dean is opening the curtains and 'Castiel' is waving his hat. Reviews/feedback are wonderful! First attempt at Supernatural, so wish me luck!
1. Literally Running In

**A/N: Let's just explain a couple of things here. 1) I have this miraculous ability of having written while having seen almost nothing of Supernatural (except for season 9 cause I'm all caught up on that). 2) Basically any interpretation I've put down here I've gotten from fanfiction and Tumblr. 3) First Supernatural thing posted here. Thank God for Tumblr. **

**Anywho, any feedback on this one'd be good because this thing was floating around on Tumblr and then it turned into a Casablanca thing. **

* * *

"My brother's coming into town."

Castiel Novak looked up from where he was cleaning glasses. "Isn't that a good thing?" He spun the glass with one hand, the other holding the rag he was cleaning it with.

Sam Winchester smiled sadly at the glass in his hands. "Not with Dean. He's always in some kind of trouble – or some kind of trouble's following him." Castiel nodded understandingly, refilling Sam's drink with his free hand, the other putting away the glass before resting on the bar. "Bobby, Bobby Singer – he told me on my way over here."

Absentmindedly, Castiel nodded again before something the younger Winchester had said caught his attention. "Dean?" Sam nodded, staring into his drink. The bartender paused for a long moment before resting both of his hands on the bar. "I knew a guy named Dean once."

"Really?" That had perked the young lawyer up.

The ghost of a smile passed over Castiel's face. "Yes. We were very close at one point." The bartender's mind started drifting, back to when it had all started when he realized Sam was still looking at him expectantly. "It is of no importance now," Castiel said quickly, pulling out a dirty glass and beginning to clean it with his rag.

Suddenly, the sounds of someone being chased could be heard through the bar's open doors. The sweltering summer hit Sam and Castiel as they quickly abandoned their spots at the bar in favor of looking outside to see who was being chased. "Damn mobsters," Sam muttered under his breath, earning a nod from Castiel. As the chase came closer to Castiel's bar, the brunette noticed his customer automatically reaching for the gun at his side...which he no longer carried. The figure being chased suddenly rammed into Sam, forcing both of them farther into the bar, knocking a table over in the process. Castiel's entire stance changed as he moved to fill his doorway, preventing the mobsters from entering and most likely killing whoever was now laying on the floor of his bar. Seconds after Castiel had re-adjusted himself, the mobsters appeared at the door.

"Move," the thug in the front of the pack demanded, his hand already resting on his weapon.

In the seven or so seconds it had taken Castiel to take his current position, his entire demeanor had become cold and hard, ready to withstand whatever these idiot mobsters had to offer. "No," he said, otherwise not moving a muscle. Some of the minion mobsters behind their leader began to get the idea, slowly inching away inconspicuously. Upset and impatient, the head mobster there moved to go around Castiel. The brunette held an arm out to stop him, not flinching when he felt the cold metal rest against the inside of his arm. "I'm not going to move," he stated, "until you and your boys leave my place and never come within then feet of it ever again."

The mobster grinned darkly, going toe to toe with Castiel. "Do you have any idea of who I am?" His eyes glinted dangerously, never shying away from the bartender's.

Castiel half-smiled, making a chill run down the leader's spine. "I believe you do not know who _I_ am." He took a moment to be dramatic, blue eyes flickering over the group before returning to the man in front of him. "You are part of Crowley's group." His voice lowered to a raspy dark whisper. "I can end your lives without even lifting a finger." The dark brunette looked over the group again, internally nodding at the terrified faces looking back at him. "Now," he began. "Leave." Within fifteen seconds, the street in front of Castiel's bar was empty. The bartender allowed himself a moment to breathe before closing his doors and hanging up his CLOSED sigh. Castiel then walked to where Sam and the mystery man were. Carefully, he shook the younger Winchester's shoulder, painfully aware that the sheer force of them landing on the hard floor probably knocked them both out.

Apparently Sam was in better condition than he though, surprising him by slowly blinking his eyes. "Castiel? What happened?" He attempted to sit up, groaning as he did.

"You were run into and knocked over by the man whom we heard being chased around."

Sam groaned again, this time finding his feet. "Yeah well, I think I figured out who that guy was." He huffed out a sigh, looking down at the unconscious figure. "Hey, Castiel, can he stay here? I mean, I seriously doubt he'll be able to get out to his hotel in this state."

Castiel nodded. "Is he trustworthy?" He carefully eyed the unconscious man.

With a laugh, Sam nodded. "He's my brother." The bartender nodded again, this time understandingly. There had been a time once where Castiel would have trusted his family to Hell and back. Nowadays, he was reasonably sure they'd kill him if they even saw him. Sam pulled him out of his thoughts. "I can carry him wherever you're letting him stay."

"Yes." Castiel began leading Sam to the only bedroom in the bar. "He may stay in here for the evening." He looked back at Sam, who had a curious expression on his face before he decided it wasn't worth being rude.

Five minutes later, the two of them were at the bar again. "So, this guys you knew." Sam segued after a long round of silence. "What made him memorable?" Confused, Castiel cocked his head to the side slightly, making Sam huff out a laugh. "I mean, you've probably met dozens of people in your life. What makes this guy – Dean – so memorable?"

A smile ghosted over Castiel's face again. "He pulled me out of a very dark time in my life and put me on the correct path as payment for saving his life." He caught the confused look on Sam's face. "I was in the same groups as those mobsters we saw earlier. It is not a particularly fond time of my life." Castiel stood up straight, obviously about to change topics. "Will you be staying to watch over your brother?"

Sam shook his head. "Nah. I trust you to watch over my big brother, Castiel. I know you don't get much sleep, and honestly I'm exhausted." He stood, pulling his suit jacket back on. "I'll come by tomorrow to check on the two of you though. See ya tomorrow." With a wave, Sam left.

Castiel sighed before downing a shot of whiskey that practically burned his throat. "Dean Winchester, huh?"

There was a vague shuffling noise and a clatter from the direction of his bedroom. Castiel quickly capped the bottle and put it away. Before he finished, he heard a wry chuckle. "So, this is what you decided to do with yourself?"

That was not possible. That was so _very_ not possible. He'd looked at him earlier. There was no way... "Dean?" Castiel found himself turning to look at the man, hope rising in his chest.

Dean Winchester smiled back at him. "Hey Cas. Long time no see."

* * *

**A/N: So? Hate me for it? Love it? I've actually gotten the majority of the second chapter written if anyone's interested...  
**


	2. Not The Happiest Reunion

The warm flutter in Castiel's chest was quickly squashed as the brunette remembered the circumstances under which they last met. Dean read the hurt that replaced the hope on Castiel's face and grimaced. "Listen, I know I should've told you…"

"Six years. Six years out of the game. Six years and not a single word since you pulled me out of the game and left me on my own to stay out."

Dean sighed. "Cas, listen to me."

"Tell me one good reason I should, Dean Winchester, P. I. If you haven't noticed, I am doing okay with no word from you. I have a job, money, and not much to worry about except for the kids who try to come into _my_ bar when _you_ run right in here and back into my life -"

"Cas, I'm getting married." That shut Castiel up. Dean felt the bottom of his stomach drop as Castiel's gaze on him hardened and he prepared himself for the attack.

Turned out not to be the attack he was expecting. "Congratulations." Castiel turned back towards the bar, hiding his face from Dean. "Would you like me to pour the groom a shot to get over his nerves and get the hell out of my bar?"

It wasn't the closed off stance that Castiel had taken that made Dean take a step back. It was the fact that the bartender's shoulders were shaking. Castiel must've known how much that would have hurt Dean because this closed off stance and show of only pain hurt the P.I. more than any blow ever could have.

If there was ever a thing Dean couldn't stand to see happen, it would be to see the ones he cared about most in any form of pain, especially if he was the one causing their pain.

Dean looked away from Castiel, his walls going up again. "Look, I'd better...I'm just gonna go." He sighed before walking towards the front door. "If Sam asks where I am tomorrow, you can tell him I've gone back to my hotel."

Castiel chuckled bitterly. "Of course you would care more about what your brother thinks happened to you than you would if I knew what happened to you." Dean frowned and turned back to the dark brunette, taking long strides to the bar.

"What did I do wrong, Cas? You gonna tell me or am I gonna have to guess?"

He didn't turn around and meet Dean's searching green eyes, the ones that wanted to figure out _so badly_ what he'd done wrong. Castiel didn't move. "Leave my bar alone." Dean frowned, his face otherwise unreadable. He didn't say another word as he left the bar, making sure to slam the door behind him as he did.

Castiel hung his head, letting out a long sigh. He relaxed his posture for a moment before getting up and locking the bar door. He shuffled to the door instead of walking, which only served to make him more sad. Once the door was locked, Castiel returned to his seat at the bar.

He picked up the bottle he'd recapped and opened it before pouring himself a glass, settling in for what appeared to be a very long night.

* * *

Several loud bangs against the bar's locked doors woke Castiel up. The brunette slowly got up from where he was lying behind the bar, blinking at all of the sunlight streaming into the large room. "Castiel!" The person banging against the door obviously wasn't going to let up unless Castiel opened the door. The moment he did, however, he began to wish he hadn't. "Castiel, is Dean okay?" Sam Winchester rushed into the bar, automatically going towards the bedroom.

"He didn't stay."

Sam stopped before turning to face Castiel. "I thought he would've wanted to stay here."

Castiel cleared his throat. "Dean and I -"

"Wait a second. He's the Dean you were talking about?" The brunette nodded.

"Dean and I have a…the last time we met, six years ago, it did not end very well." Sam held his arms out, waiting for a continuation or an explanation. "If you would care to learn the entire story, I suggest you ask him. He went back to his hotel last night after our…conversation," Castiel finished, his stance making it clear that he wasn't going to be the one to explain it to the younger Winchester.

A frown crossed Sam's face. "Thanks, Castiel. I'll make sure to ask Dean when I go and check on him." He turned and began to leave the bar. "I do plan on finding out what happened. And I'm not talking about last night," he added just as he was about to walk out the door.

Castiel took a deep breath, watching Sam leave. "Today is certainly going to be interesting."

* * *

Dean pulled the pillow over his head to block out the knocking on his hotel room door. When he figured that wasn't going to work, he pulled the pillow up just enough for him to glare at the door. "I'm still asleep!"

"Dean, open up. I gotta talk to you."

The blonde groaned but got up anyway. He opened the door grumpily. "What the hell, Sammy? It's not even seven yet!"

His brother looked down at him, a frown on his face or, as Dean had called it, Bitchface number nine. "Dean. You didn't stay at Castiel's bar."

Sam watched Dean's face go blank with that mask he'd perfected years before. "So that's why you're here. Cas sent you."

"No, I'm here to make sure my idiot brother didn't get injured after he rammed me into the floor of a bar yesterday. Now, let me in." Dean rolled his eyes but moved aside anyway, knowing that Sam would get in one way or another. Unfortunately, that also came with his little brother's distaste for how much Dean usually brought with him on a case. "Jeez Dean, you're getting married. You could've brought more stuff."

Dean shrugged, closing the door. "It's all I felt like bringing.." He flopped back down onto the bed. "Besides, I thought you weren't here to criticize me on my packing choices."

The brunette nodded, putting his hands on his hips. "I'm pretty sure you're gonna wanna be awake for this, Dean. I'll make coffee."

"Whoa, no!" Dean nearly jumped off the bed when he heard that. "You're coffee's terrible. _I'll_ make coffee. You can figure out what you want me to say or whatever."

His little brother suffered for a minute in silence before Dean turned back to him. Sam frowned, crossing his arms. "Well?"

Dean glanced up momentarily to look at Sam. "Well what, Sammy?"

His younger brother rolled his eyes. "What happened between you and Castiel six years ago?"

"We met," Dean replied, his heart heavy. "The entire story's not something I'm gonna tell you. Don't think you're old enough yet."

A huff sounded, a sure sign Sam was annoyed at his older brother. "Then tell me the short, clean version."

Dean looked up at Sam. From the look he was getting, he was sure Sam wouldn't leave him alone until he'd heard at least the short version. "Take a seat," Dean said, pulling a chair out for himself. "You wanted the short version. It's still gonna take a while." He sighed, a deep thing emanating from the same place it had six years earlier. "All right then. I was doing some work for a guy who'd stopped by the office the day before. It led to the mob and I was getting chased down a street after being grazed by a bullet. Didn't do me any harm, but it sure hurt like hell."

* * *

Dean Winchester's coat flew behind him like a cape as he ran down the poorly lit street, raindrops falling on to his overcoat and fedora. He spotted a corner and dashed just around it, taking a minute to catch his breath. Footsteps ran closer to his hiding place, making him tense. Dean relaxed when they ran past him. He took a moment to look at his arm and assess the graze he'd gotten that had led to his running. "I could aid you in treating that wound," a deep gravelly voice said from further down the corner.

The blonde nearly jumped when he heard the mystery man talking to him, automatically going for his gun. "Damn son of a bitch," he muttered, his eyes finally resting on the man. Seconds later, Dean flinched as rain began to hit his wound and the adrenaline wore off.

"That is an inaccurate description of me. My mother was not a female dog," the mystery man stated, the light not enough for Dean to see his face. "I am willing to offer my services in the treatment of your wound."

Dean chuckled wryly. "Yeah? And why would you do that?"

"Because I was sent to kill you." He merely raised an eyebrow in response as if to say 'Really?'. The other man shifted on his feet. "Would you prefer if I left you to tend to the wound on your own?"

A deep sigh sounded from somewhere deep inside Dean. "I guess I'll take you up on that offer."

* * *

Sam sat back into his chair. "So you went with the guy sent to kill you to wrap up your arm."

Dean sat up in his chair. "I know, but I figured if I let this guy help me then I might end up living longer than if he let me wrap my arm up by myself. It wasn't like I could head back to the office and get you to help me." Sam winced at that, fully aware that if he hadn't been off at school at the time then none of this would've happened in the first place.

The brunette nodded, conceding to his brother's reasoning. "All right, you went with the guy sent to kill you. But, that was Castiel, wasn't it? How did you two even get onto a first name basis?"

A chuckle sounded through the room. "It wasn't my fault, I swear."

* * *

Dean looked the guy up and down, trying to read him and/or figure out how much longer he was gonna live for at this rate. After a second or two, the man chuckled. "What?" He attempted to at least sound threatening while he was in his very vulnerable state.

The man shook his head. "It is of no importance. I merely find it amusing that you, as a private investigator, are trying to get information from me, even as I am assisting you." Even through the dim light, Dean could see the little smile stuck to the man's face. "It's Castiel, if you were wondering."

"What's Castiel?"

"My name," the man replied nonchalantly. Dean tilted his head, looking at the man - Castiel - strangely. "I thought it was proper to tell you my name since I already know yours. I may have been sent to kill you but I still have my manners, Mister Winchester."

* * *

Sam half-smiled, not quite believing what he was hearing. "So Castiel, _Castiel_ mind you, the guy sent to kill you, was the one who introduced himself to you while helping you wrap up your arm after being grazed by a bullet." Dean nodded, going through the entire statement in his head a couple of times to make sure Sam got everything right.

"Yeah, sounds about right."

His little brother shook his head, a grin on his face. "I knew that Castiel was strange but _man_, that is really weird."

* * *

**A/N: So? Anybody happy with the way that turned out? Reviews/feedback? Pretty please with a 40's Dean and Cas?**


	3. His Fiancé and A Car Named Baby

The two brothers were disrupted by a series of knocks on the door. Dean groaned, making Sam look at him strangely. "I forgot. Lisa's coming over."

"Shouldn't you be happy about that?"

Dean frowned at Sam. "Normally, that'd be great, but seriously, could her timing be any worse?" Sam rolled his eyes at his brother before giving him Bitchface number three. "Sammy, seriously? You're the one who asked me!"

"Yeah, and she's _your_ fiancé, Dean." Dean slumped into his chair. "Go talk to her. You'll probably be with her for a while, so I'll go ask Castiel what happened from there." At that Dean sat up straight in his chair, making Sam chuckle. "Y'know, I can't tell whether you're more afraid that your fiancé is here while you're explaining a previous relationship or that I just suggested that I ask Castiel about the rest of the story."

The blonde glared at Sam. "It ain't funny, Sam." His brother held his hands up, not very apologetic. After a moment, Dean sighed. "Alright, go ask Cas. I'm gonna let Lisa in." He stood and briefly checked his appearance in the mirror (earning himself a laugh from Sam) before opening the door. "Hey, Lisa."

"Dean!" Lisa Braeden smiled at her fiancé. "I was beginning to get worried when you didn't answer immediately." After a second she noticed Sam. "You must be Sam," she said, moving past Dean to greet his brother, who stood when Dean opened the door. "Sorry if I'm interrupting something. I was just coming to get Dean for a couple of things for the wedding."

Sam shook his head while shaking Lisa's hand. "No, you're not interrupting anything. I was actually just leaving. Have fun. I'll have to remember to get Dean to bring me over for dinner at some point before the two of you get married."

* * *

"Castiel! Let me in!"

The bartender groaned, his head throbbing. After a brief internal debate, he stood and slowly walked over to the bar doors. "What do you want?"

Sam took a moment to look Castiel up and down before realizing what was off about the dark brunette. "Are you...drunk?"

Castiel shrugged. "Most likely not any more." He looked up at Sam, squinting in the sunlight. "Why are you here?"

Half-smiling as Castiel's misfortune (and by misfortune I mean obvious hangover), Sam decided to help the bartender by closing all of the bar's blinds. "Dean's fiancé came over while I was talking to him about you. She wanted to take him away for stuff for their wedding so I decided to come back and ask you about what else happened." The taller brunette sat down at the bar, waiting for Castiel to join him.

Sighing, Castiel re-locked the bar's doors before standing across from Sam behind the bar. "Where did the two of you leave off?"

"You'd just told Dean your name."

Castiel took a moment to glare at Sam. "I have a feeling that you made a rude comment about that situation." Sam shrugged, doing moderately well to hide his smile. "After I helped Dean, we each went our separate ways. I knew that Dean wouldn't just give up on a case, even after the events that led to our meeting, so I forewarned your brother that we would meet again. However, it seemed that Dean was not expecting me to reappear as I did."

* * *

Dean was walking back to his office after a brief grocery run (Sammy'd sent a telegram that had only said "healthy food") when he noticed someone standing in front of his car. His precious car, which Sam could attest to, because sometimes his older brother referred to it as "Baby", leading to an eye roll from the taller of the two brothers. So, Dean decided to do the easiest course of action when his Baby was involved.

"If you touch that car I swear I will shoot you without hesitation." Whoever it was obviously believed him because they backed away slowly with their hands up. "Now who the hell are you and do you know who's car that even is?" Dean didn't move as he watched the man turn around, not allowing the surprise to show on his face. "Castiel?"

There was the slightest hint of a smile on Castiel's face as he turned to Dean. "Hello, Mister Winchester. I did tell you that we would meet again."

Dean holstered his gun. "Yeah but I wasn't expecting to shoot you for touching my car."

"You weren't in the office when I stopped by."

The blonde rolled his eyes. "Castiel, what are you doing here?"

Castiel shrugged. "I merely -"

"- and I swear if you finish that sentence with 'came to see you', I will pull out my gun and shoot you." The dark brunette shut his mouth, holding his hands up in surrender. "Now what're you actually doing here?" Dean crossed his arms, determinedly glaring at Castiel and not thinking about how happy he was to see him again.

After a moment, Castiel spoke again. "I came to see if you had any intention of further investigation of the case involving the Novak gang." The blonde was silent, which Castiel took as an affirmative. "The head of the gang, Michael Novak, is very dangerous. The majority of the rumors about him involve violent deaths."

Dean hummed in agreement. "Sounds like you know the guy." Unfortunately for Castiel, Dean's people reading skills weren't as bad as his so the P.I. didn't missed the uncomfortable foot-shifting the dark brunette did. Letting out a little "huh", Dean decided to ignore it for the time being and turn the conversation back to the reason Castiel came to see him. "Sorry, Castiel. The client hired me to see the end of this case so they can get their closure."

Castiel cocked his head to the side, curious. "Is the client someone you know very well?"

"What? No." Dean shook his head. "Why d'you ask that?"

The dark brunette blinked at the sudden question. "It seems as though you're taking this case very personally."

Dean shook his head again. "It's my job to help people find closure for cases they have interest in or ones that relate to their family in some way. Sometimes it isn't murder and is just some boring family history thing."

Castiel nodded. "Are you always this...persistent in the investigation of these cases?"

The P.I. shrugged. "Sometimes, when the family's really worried." He glanced at his watch, obviously trying to change topics. "I gotta go. Don't get paid just to stand around." Castiel nodded again. "See ya, Cas." It was a slip of the tongue, but Castiel found that he didn't really mind it. Actually, he found it sort of comforting. With a little smile, the dark brunette turned away from Dean's office building and began to walk away, completely missing Dean's glance back at him.

* * *

Sam leaned away from the bar, trying to crack his back. "Dean seriously thought you were gonna hurt his car?"

Castiel shrugged. "He seemed very protective of it."

Laughing, the younger Winchester leaned back onto the bar. "Dean loves that car. Seriously, he threatens people who just walk past it too close." He shrugged. "Never did understand why. Still don't actually." Sam frowned, before shaking it off. "Drinks?" Castiel nodded before pulling out two shot glasses and a bottle of whiskey. Sam nodded after the bartender filled both glasses. "I see why Dean talked about you so fondly now."

* * *

**A/N: WHOA WHOA WHOA I AM SO SORRY I LOVE YOU ALL I TOTALLY FORGOT TO WRITE ONE OF THESE OH MY GOD WHY NIGHT VALE STOP DISTRACTING ME  
**

**Okay, now that that's over with. Hi! Sorry it's been so long. School's been insane and this is winter break with my family wanting me to stay off of the computer (like that's gonna happen). Belated happy holidays to everyone and an early Happy New Year because I doubt I'll be updating again that soon. **

**So, overall, was the chapter worth it or would you still like to murder me for waiting this long and not tackling a huge writer's block earlier? Thank you all!**


	4. Whiskey and the Novak Gang

After an admission like that, Castiel found himself unable to say anything and had a hard time hiding the stupid little grin that crossed his face as Sam downed his first whiskey shot. "Anyway, what happened after that?"

For a split second, Castiel felt his heart sink because he thought the next thing would be _that_ before he realized that it was something else first. "Dean did some research as to who I am and confronted me about my connection to the Novak gang. It was his version of payback for my surprising him."

* * *

"So, you're part of the Novak gang, huh?"

Castiel spun on his heel to catch the man, his hand automatically going for his handgun. His fingers curled around the familiar grip as his eyes landed on a man he never thought to see again. "I should've known that you would discover more information on me, Mister Winchester."

Dean's features were set, his face a perfectly blank mask. Castiel watched his eyes attempt to land on a single emotion. Unfortunately, they decided on disappointment, but not before the brunette saw something he could've sworn was curiosity. "You know how the old saying goes. 'Curiosity killed the cat'. Thought, I guess that applies to my line of work in general. You already knew that thought." The blonde observed Castiel for a moment. "I never figured I'd live long enough to meet a member of the Novak family."

His features were schooled except for the tiniest narrowing of his eyes for a second. "It would be highly presumptuous of you if you think I'm a relative of the Novaks." Castiel cocked his head to the side slightly. "What makes you think I'm a Novak?"

The P.I. grinned a little. "I'm a high profile target in the Novak's books. They wouldn't just send anyone to kill me, not if I know them, and I do."

Castiel was quiet for a few long moments. "Why do you believe that?"

"I've got my sources."

The brunette's eyes flicked over Dean's face, searching for answers. "Gabriel," he finally said. "He's the only one I know of who would be willing to cooperate with you besides Anna or Balthazar."

Dean stared at Castiel, less amiable then he had been when they met last. "What makes you think any of them would cooperate with me, especially since I'm a well known enemy of the Novaks?"

"You're giving yourself too much credit for one. Another could be that while they act as if they do not care, they are just as human as anyone else." Castiel narrowed his eyes again when Dean let out a little "Huh". The brunette felt his body tense in preparation for a fight. "What?"

The blonde shook his head slightly. "I'm just trying to decide if you're putting yourself in that group or not. Either that or you're just really close to those three members."

* * *

"So Dean sought you out," Sam summarized as Castiel downed a shot of whiskey.

The bartender nodded, his throat burning slightly. "Hunted down would be the more accurate term. Apparently he found all of the information he could about the Novak gang, including where their most common meeting places were."

Sam nodded. "But Dean was right, You are a part of the Novak family."'

Castiel sighed and nodded. "My eldest brother was the leader at that point in time. I have no idea if he still is. The other three I mentioned - Anna, Balthazar and Gabriel - are also relatives of mine. Gabriel is my older brother. Anna and Balthazar are my cousins. Unfortunately, they also suffered from my cooperation with your brother."

"Why? I mean, no offence, but you're the one who worked with Dean, not them. They shouldn't of been punished or whatever happened." Sam paused, taking a second to look at Castiel's expression. "Your brother found out."

Castiel nodded again. "Before I was punished for my cooperation with Dean, he told me that they were foolish in assisting me in my cooperation because they would be punished as well. I have not seen any of them since and believe them to be dead on his orders."

Sam was silent for a moment. "Could they have actually helped him without you knowing it?"

The bartender shrugged. "It's possible although unlikely."

A series of knocks against the bar doors startled them out of their conversation. Cautiously, Sam opened the door after unlocking it with the key Castiel had left on the bar. "Dean."

His older brother half-smiled. "Hey, Sammy. Can I come in?" Sam nodded after glancing back at Castiel to get the bartender's approval. Dean took a deep breath in before walking into the bar. "Hey, Cas."

Castiel nodded curtly to the P.I. "Dean."

Sam quickly closed and locked the door before returning to his seat at the bar. "We were just wondering about something Castiel said."

Dean looked at the dark brunette, surprised. Castiel nodded again. "It was when you confirmed with me that I was a Novak."

"So this is about whether I ever met Gabriel, Anna or Balthazar, right?" Sam didn't look surprised, but Castiel did. The P.I. grinned at the bartender. "You thought I forgot about it? Shame on you, Cas." Dean nodded, sitting at the bar beside Sam, across from Castiel. "I actually did meet them because they got curious."

* * *

"Well, Cassie wasn't lying when he told me you would be prepared to shoot me if you ever met me."

Dean watched the man step out of the shadows, tossing a piece of candy into his mouth. "And who the hell are you that he would be so certain I'd shoot?"

The man scoffed, a grin spreading across his face. "I go by The Trickster on the streets. Cassie knows me by my real name though, since we _are_ related. Name's Gabriel Milton." He waved a hand at Dean, practically ignoring the gun pointed at him. "Put that thing away. It's not like I'm gonna attack you or something." Hesitantly, the P.I. holstered his sidearm. "Alright, now we can talk." Gabriel sat down behind Dean's desk, sticking his feet up on the sturdy wood.

"What the hell does The Trickster want with me?"

Gabriel grinned, tilting his head to the side. "You are adorable. Now I see why Cassie couldn't resist talking about you. Speaking of Cassie, I'm surprised you know who I'm even talking about." Dean rolled his eyes, resisting the urge to either pull out his gun and shoot Gabriel or punch him. "It's not like anyone else calls Castiel by a nickname."

The blonde paused for a moment. "I call him Cas in my head."

He felt himself being scrutinized when Gabriel looked up at him again. "Well, I'll be damned. A P.I. who actually cares about the cases he works." After a second, Gabriel was off again. "Anyway, that's not what I came by to talk about, Dean-o. I was kinda wondering how the hell you and Cassie got to be all buddy-buddy out of the blue."

Dean cleared his throat. "I was being shot at, Cas had a conscience."

Gabriel narrowed his eyes for a second. "Cassie wasn't even supposed to be there. I'd taken him out drinking and got distracted. I assumed he'd gotten home on his own."

* * *

"Whoa, whoa, whoa, stop there, Dean." Sam held his hands up, a grin on his face. "Castiel was out drinking with his cousin?"

Dean shrugged. "I never did get confirmation on whether what Gabriel had been telling me was true or not." He looked over at Castiel, who was now sitting across from him as they'd moved to one of the tables in the bar. "Was Gabriel right?"

Castiel didn't meet Dean's eyes. "Please continue explaining what happened."

* * *

"Anyway," Gabriel continued. "I'm here to make sure that you don't go do something stupid like break his heart or anything."

The blonde rolled his eyes. "It's not like I've asked him out or anything."

Gabriel let a huge shit-eating grin cross his face. "Oh, I wouldn't say that. But, you did track him down and confront him about being a Novak, especially Michael's little brother." He nodded. "Yeah, that's not something a couple does at all. Confrontations and the whole drama? That's a regular mystery, not a cheesy romance novel." Dean rolled his eyes again. Gabriel tilted his head, this time curious. "Huh. You really don't get it." He stood stretching. "Was nice talking to you, Winchester, but I gotta get going. See ya around."

Dean watched Gabriel saunter nonchalantly out of his office. "That was the weirdest thing that's happened to me all day."

* * *

**A/N: I'm close enough to New Years to say Happy New Years again. HAPPY NEW YEARS ALL! I'm happy I actually had the majority of this one down earlier otherwise it might've been a really long time before I updated again. Anywho, did you all like it? Even the random Gabe? I'll get to Balthazar and Anna later...ish. Honestly I have no clue whether I'm writing them correctly or not so I'm just sitting her with my fingers crossed. Reviews and feedback are loved!**


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